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Hydrogen-atom transfer reactions from ortho-alkoxy-substituted phenols:An experimental approach
The role of intramolecular hydrogen bonding (HB) on the bond-dissociation enthalpy (BDE) of the phenolic O-H and on the kinetics of H-atom transfer to peroxyl radicals (kinb) of several 2-alkoxyphenols was experimentally quantified by the EPR equilibration technique and by inhibited autoxidation studies. These compounds can be regarded as useful models for studying the H-atom abstraction from 2-OR phenols, such as many lignans, reduced coenzyme Q and curcumin. The effects of the various substituents on the BDE(O H) of 2-methoxy, 2-methoxy-4-methyl, 2,4-di-methoxyphenols versus phenol were measured in benzene solution as -1.8; -3.7; – 5.4 kcalmol-1, respectively. In the case of polymethoxyphenols, significant deviations from the BDE(OH) values predicted by the additive effects of the substituents were found. The logarithms of the kinh constants in cumene were inversely related to the BDE(O-H) values, obeying a linear Evans-Polanyi plot with the same slope of other substituted phenols and a y-axis intercept slightly smaller than that of 2,6-dimethyl phenols. In the cases of phenols having the 2-OR sub-stituent included in a five-membered condensed ring (i.e, compounds 9-11), 11both conformational isomers in which the OH group points toward or away from the oxygen in position 2 were detected by FTIR spectroscopy and the intramolecular HB strength was thus estimated. The contribution to the BDE(O-H) of the ortho-OR substitu-ent in 9, corrected for intramolecular HB formation, was calculated as -5.6 kcal mol-1. The similar behaviour of cyclic and non-cyclic ortho-alkoxy derivatives clearly showed that the preferred conformation of the OMe group in ortho-methoxyphenoxyl radicals is that in which the methyl group points away from the phenoxyl oxygen, in contrast to the geometries predicted by DFT calculations.
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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H2335O – PubChem